Methyl iodide → HCID 15457460, compound

HRID 1601132Notes

Reaction equation

HRID 1601132 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4](=[S:21])[NH:3]1.[H-].[Na+].I[CH3:25]>O1CCCC1>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:4]([S:21][CH3:25])=[N:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15457459HCID 15457459, compound

Product 1

HCID 15457460HCID 15457460, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 900 mg of crude 2-methyl-4-(2-phenoxyphenyl)-5-thioxo-1,2,4-triazolidin-3-one in 50 mL of tetrahydrofuran was treated with 150 mg of sodium hydride (60% oil dispersion). After 5 minutes, 0.5 mL of iodomethane was added, and the mixture was stirred at ambient temperature overnight. The solid was removed by filtration and the filtrate concentrated to an oil. The oil was partitioned between ether and 1N hydrochloric acid solution. The organic phases were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was triturated in hexane/n-butyl chloride to afford 530 mg (56%) of the title compound of Step C, m.p. 129-130° C.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate concentrated to an oil
  3. customThe oil was partitioned between ether and 1N hydrochloric acid solution
  4. dry with materialThe organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated in hexane/n-butyl chloride

Sources & evidence

ORD record
ord-a9392edb33464fe9af72041a330eb77f
Source dataset
uspto-grants-1999_11
Patent number
US05977149

Reaction notes

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